Tunable Gold(I)-Catalyzed [4+3] Cycloaddition for Divergent Synthesis of Furan-Fused N,O-Heterocycles

被引:31
|
作者
Zhang, Shouzhi [1 ]
Tang, Aijie [1 ]
Chen, Panpan [1 ]
Zhao, Zhiqiang [1 ]
Miao, Maozhong [1 ]
Ren, Hongjun [1 ,2 ]
机构
[1] Zhejiang Sci Tech Univ, Hangzhou, Peoples R China
[2] Taizhou Univ, Taizhou, Peoples R China
关键词
DIASTEREOSELECTIVE 1,3-DIPOLAR CYCLOADDITION; 1-(1-ALKYNYL)CYCLOPROPYL KETONES; 3-COMPONENT REACTION; CATALYZED REACTIONS; ALLENYL KETONES; GOLD CARBENES; METAL; 2-(1-ALKYNYL)-2-ALKEN-1-ONES; NUCLEOPHILES; GENERATION;
D O I
10.1021/acs.orglett.9b04312
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
By choosing suitable ligand-directed gold catalysts, two types of gold-containing all-carbon 1,4-dipoles could be generated selectively from the gold(I)-catalyzed cycloisomerizations of allenyl ketones bearing a cyclopropyl moiety, which undergo [4 + 3] cycloadditions with nitrones to produce two regiomers of furan-condensed N,O-seven-membered rings in moderate to excellent yields highly selectively.
引用
收藏
页码:848 / 853
页数:6
相关论文
共 50 条
  • [41] Silver(i)-catalyzed selective hydroalkoxylation of C2-alkynyl quinazolinones to synthesize quinazolinone-fused eight-membered N,O-heterocycles
    Kong, Xiang-Fei
    Guo, Xiu-Yun
    Gu, Zi-Yu
    Wei, Lin-Su
    Liu, Lu-Lu
    Mo, Dong-Liang
    Pan, Cheng-Xue
    Su, Gui-Fa
    ORGANIC CHEMISTRY FRONTIERS, 2020, 7 (15) : 2055 - 2062
  • [42] N-Heterocyclic Carbene (NHC)-Catalyzed [4+3] Cycloaddition to Synthesize 4-Aminobenzoheptenolactons
    Dai Chunbo
    Xia Siqi
    Chen Xiaoyu
    Yang Limin
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2023, 43 (03) : 1084 - 1090
  • [43] Computational study on gold-catalyzed (4+3) intramolecular cycloaddition of trienyne: mechanism, reactivity and selectivity
    Li, Meng-Ru
    Wang, Gui-Chang
    RSC ADVANCES, 2016, 6 (77) : 73454 - 73468
  • [44] Copper-catalyzed (4+3)-cycloaddition of 4-indolylcarbinols with aziridines: stereoselective synthesis of azepinoindoles
    Kar, Subhradeep
    Maharana, Prabhat Kumar
    Maity, Swagata
    Trivedi, Vishal
    Punniyamurthy, Tharmalingam
    Chemical Communications, 2024, 60 (83) : 12008 - 12011
  • [45] Palladium-catalyzed [4+3] dearomatizing cycloaddition reaction of N-iminoquinolinium ylides
    Dai, Wenhao
    Li, Chunpu
    Liu, Yichu
    Han, Xu
    Li, Xingjun
    Chen, Kaixian
    Liu, Hong
    ORGANIC CHEMISTRY FRONTIERS, 2020, 7 (18) : 2612 - 2617
  • [46] One-Pot Synthesis of Fused N,O-Heterocycles through Rh(III)-Catalyzed Cascade Reactions of Aromatic/Vinylic N-Alkoxy-Amides with 4-Hydroxy-2-Alkynoates
    Xu, Yuanshuang
    Li, Bin
    Zhang, Xinying
    Fan, Xuesen
    ADVANCED SYNTHESIS & CATALYSIS, 2018, 360 (14) : 2613 - 2620
  • [47] Gold(I)-Catalyzed Intramolecular SEAr Reaction: Efficient Synthesis of Isoxazole-Containing Fused Heterocycles
    Morita, Taiki
    Fukuhara, Shintaro
    Fuse, Shinichiro
    Nakamura, Hiroyuki
    ORGANIC LETTERS, 2018, 20 (02) : 433 - 436
  • [48] Enantioselective Formal Synthesis of (-)-Englerin A via a Rh-Catalyzed [4+3] Cycloaddition Reaction
    Xu, Jing
    Caro-Diaz, Eduardo J. E.
    Theodorakis, Emmanuel A.
    ORGANIC LETTERS, 2010, 12 (16) : 3708 - 3711
  • [49] Gold(I)-Catalyzed Benzylic C(sp3)-H Functionalizations: Divergent Synthesis of Indole[a]- and [b]-Fused Polycycles
    Greiner, Luca C. C.
    Arichi, Norihito
    Inuki, Shinsuke
    Ohno, Hiroaki
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2023, 62 (03)
  • [50] [4 + 3] Cycloaddition of ketenimines with furocarbenoids: Divergent and efficient synthesis of fused cycloheptatriene and tropone scaffolds
    Jin Wang
    Zhaoyang Li
    Shengxin Bai
    Qinghua Zhou
    Tengteng Wu
    Zhongyan Hu
    Xianxiu Xu
    Chinese Chemical Letters, 2023, 34 (05) : 258 - 262